EP1496074A1 - Use of a mixture of bisethoxylated bisphenol a / diethoxylated resorcinol (dianol 220/HER) as chain extender for polyurethane elastomers compositions - Google Patents

Use of a mixture of bisethoxylated bisphenol a / diethoxylated resorcinol (dianol 220/HER) as chain extender for polyurethane elastomers compositions Download PDF

Info

Publication number
EP1496074A1
EP1496074A1 EP04102986A EP04102986A EP1496074A1 EP 1496074 A1 EP1496074 A1 EP 1496074A1 EP 04102986 A EP04102986 A EP 04102986A EP 04102986 A EP04102986 A EP 04102986A EP 1496074 A1 EP1496074 A1 EP 1496074A1
Authority
EP
European Patent Office
Prior art keywords
weight
formula
composition
mpa
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP04102986A
Other languages
German (de)
French (fr)
Inventor
Georges Soc.d'Exploitation de Prod. Da Costa
Hervé Soc.d'Exploitation de Prod Rolland
Daniel Soc. d'Exploitation de Prod Muller
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA
Original Assignee
Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA filed Critical Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA
Publication of EP1496074A1 publication Critical patent/EP1496074A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step

Definitions

  • the invention is in the field of the preparation of elastomers.
  • elastomeric polymers often involves the elongating compounds of chains whose function is to improve certain physical properties of the final polymer, such as hardness, heat resistance or hydrolysis resistance.
  • chain lengtheners most used in the preparation of elastomeric polyurethanes are butanediol-1,4 or BDO: 1,4-bis [(2-hydroxyethyl) oxy] benzene or HQEE: or resorcinol diethoxylated or HER:
  • the subject of the invention is a composition characterized in that it comprises from 0.5% by weight to 100% of a compound of formula (I): in which R 1 , R 2 , R 3 and R 4, which are identical or different, independently of one another represent a hydrogen atom, a methyl radical or an ethyl radical, n and m, which are identical or different, represent, independently of one another, a number between 0 and 10, provided that the sum n + m is greater than zero, and from 0% to 99.5% by weight of a compound of formula (II): in which R 5 , R 6 , R 7 and R 8, which are identical or different, independently of one another represent a hydrogen atom, a methyl radical or an ethyl radical, p and q identical or different are independently of each other a number between 0 and 10 provided that the sum
  • radicals: -O-CHR 1 -CHR 2 -, -CHR 3 -CHR 4 -O-, -CHR 5 -CHR 6 -O- and -CHR 7 -CHR 8 -O- represent more particularly, independently of one another the following divalent radicals: - O-CH 2 -CH 2 -, -CH 2 -CH (CH 3 ) -O-, -CH (CH 3 ) -CH 2 -O-, -CH (C 2 H 5 ) -CH 2 -O- or - CH 2 -CH (C 2 H 5 ) -O-.
  • radicals -O-CH 2 -CH 2 -, -CH 2 -CH (CH 3 ) -O-, - CH (CH 3 ) -CH 2 -O-, -CH (C 2 H 5 ) -CH 2 -O- or -CH 2 -CH (C 2 H 5 ) -O-, are distributed sequentially or randomly .
  • the subject of the invention is a composition as defined above, for which, in the formula (I), R 1 , R 2 , R 3 and R 4 each represent a hydrogen atom.
  • the subject of the invention is a composition as defined above, for which, in formula (II), R 4 , R 5 , R 6 and R 7 each represent a hydrogen atom.
  • the subject of the invention is a composition as defined above, comprising from 10% by weight to 60% by weight and preferably from 15% by weight to 55% by weight of compound of formula (I) and from 40% by weight to 90% by weight and preferably from 45% by weight to 85% by weight of compound of formula (II).
  • the subject of the invention is particularly a composition as defined above in which the compound of formula (I) is: diethoxylated bisphenol A of formula (Ia): and wherein the compound of formula (II) is diethoxylated resorcinol of formula (IIa)! and preferably a composition containing from 30% by weight to 50% by weight of compound of formula (Ia) and from 50% by weight to 70% by weight of compound of formula (IIa).
  • the subject of the invention is also the use of the composition as defined previously as a chain extender in an elastomeric formulation of polyurethanes and a method for preparing an elastomeric formulation of polyurethane from isocyanate prepolymer and an effective amount of extender chain, characterized in that said chain extender is the composition as defmie previously.
  • the subject of the invention is the use of the composition as defined above, as monomers in the preparation of saturated polyesters unsaturated, polycarbonates or epoxy resins.
  • composition E A mixture of 52% by weight of diethoxylated resorcinol and 48% by weight of weight of diethoxylated bisphenol A called composition E.
  • Formulation Formulation A (basis of comparison) Formulation I (invention) Vibrathane TM B625 (% NCO: 6029) 100 g 100 1,4-butanediol 6.41 g 0 composition E 0 7.39 g BYK TM A 530 (debulling agent) 0.5 g 0.5 g Pot life 6 minutes 21 minutes Process parameters Prepolymer temperature 85 ° C 85 ° C Extender temperature 85 ° C 85 ° C Cooking temperature 120 ° C 120 ° C Stirring time 30 minutes 30 minutes Cooking time 4 hours 4 hours Post cooking time 16 hours 16 hours ripening time 6 days 6 days Aspect of the final formulation opaque slight transparency Glassy temperature 69.7 ° C -55.7 ° C Melting temperature 169.2 ° C 157 ° C
  • composition E according to the invention as a chain extender with respect to butanediol-1,4, the product the more used in this function.

Abstract

Composition comprising 0.5-100 wt.% alkoxylated bisphenol A (I) and 0-99.5 wt.% alkoxylated resorcinol (II) is new. Composition comprising 0.5-100 wt.% alkoxylated bisphenol A of formula (I) and 0-99.5 wt.% alkoxylated resorcinol of formula (II) is new. [Image] R 1-R 8H, Me or Et; n, m : 0-10, provided that n+m is above zero; and p, q : 0-10, provided that p+q is above zero. An independent claim is also included for producing a polyurethane elastomer formulation from an isocyanate prepolymer and a chain extender which is a composition as above.

Description

L"invention s'inscrit dans le domaine de la préparation d'élastomères.The invention is in the field of the preparation of elastomers.

La préparation de polymères élastomères met souvent en oeuvre les composés allongeurs de chaínes qui ont pour fonction d'améliorer certaines propriétés physiques du polymère final, comme sa dureté, sa résistance à la chaleur ou sa résistance à l'hydrolyse.The preparation of elastomeric polymers often involves the elongating compounds of chains whose function is to improve certain physical properties of the final polymer, such as hardness, heat resistance or hydrolysis resistance.

Les allongeurs de chaíne les plus utilisés dans la préparation des polyuréthanes élastomères sont le butanediol-1,4 ou BDO :

Figure 00010001
le 1,4 -bis[( 2-hydroxy éthyl) oxy] benzène ou HQEE :
Figure 00010002
ou le résorcinol diéthoxylé ou HER :
Figure 00010003
The chain lengtheners most used in the preparation of elastomeric polyurethanes are butanediol-1,4 or BDO:
Figure 00010001
1,4-bis [(2-hydroxyethyl) oxy] benzene or HQEE:
Figure 00010002
or resorcinol diethoxylated or HER:
Figure 00010003

Dans le cadre de ses recherches sur les composés polyalcoxylés, la demanderesse, a développé un nouvel allongeur de chaíne qui améliore les propriétés physiques des polymères polyuréthanes.
   c'est pourquoi l'invention a pour objet une composition caractérisée en ce qu'elle comprend
   de 0,5 % en poids à 100 % d'un composé de formule (I) :

Figure 00020001
dans laquelle R1, R2, R3 et R4 identiques ou différents, représentent indépendamment, les uns des autres un atome d'hydrogène, un radical méthyle ou un radical éthyle,
n et m identiques ou différents, représentent indépendamment l'un de l'autre un nombre compris entre 0 et 10 étant entendu que la somme n + m est supérieure à zéro,
et
   de 0% à 99,5 % en poids d'un composé de formule (II) :
Figure 00020002
dans laquelle R5, R6, R7 et R8 identiques ou différents, représentent indépendamment, les uns des autres un atome d'hydrogène, un radical méthyle ou un radical éthyle,
p et q identiques ou différents représentent indépendamment l'un de l'autre un nombre compris entre 0 et 10 étant entendu que la somme p + q est supérieure à zéro.In the context of its research on polyalkoxylated compounds, the Applicant has developed a new chain extender which improves the physical properties of polyurethane polymers.
this is why the subject of the invention is a composition characterized in that it comprises
from 0.5% by weight to 100% of a compound of formula (I):
Figure 00020001
in which R 1 , R 2 , R 3 and R 4, which are identical or different, independently of one another represent a hydrogen atom, a methyl radical or an ethyl radical,
n and m, which are identical or different, represent, independently of one another, a number between 0 and 10, provided that the sum n + m is greater than zero,
and
from 0% to 99.5% by weight of a compound of formula (II):
Figure 00020002
in which R 5 , R 6 , R 7 and R 8, which are identical or different, independently of one another represent a hydrogen atom, a methyl radical or an ethyl radical,
p and q identical or different are independently of each other a number between 0 and 10 provided that the sum p + q is greater than zero.

Dans les formules (I) et (II) telles que définies précédemment, les radicaux :
-O-CHR1-CHR2-, -CHR3-CHR4-O-, -CHR5-CHR6-O- et -CHR7-CHR8-O-, représentent plus particulièrement, indépendamment les uns des autres un des radicaux divalents suivants :
- O-CH2-CH2-, -CH2-CH(CH3)-O-, -CH(CH3)-CH2-O-, -CH(C2H5)-CH2-O- ou - CH2-CH(C2H5)-O-.In the formulas (I) and (II) as defined above, the radicals:
-O-CHR 1 -CHR 2 -, -CHR 3 -CHR 4 -O-, -CHR 5 -CHR 6 -O- and -CHR 7 -CHR 8 -O-, represent more particularly, independently of one another the following divalent radicals:
- O-CH 2 -CH 2 -, -CH 2 -CH (CH 3 ) -O-, -CH (CH 3 ) -CH 2 -O-, -CH (C 2 H 5 ) -CH 2 -O- or - CH 2 -CH (C 2 H 5 ) -O-.

Au sein de chacun des groupes -[O-CHR1-CHR2]n-, -[CHR3-CHR4-O]m-, -[CHR5-CHR6-O]p- ou -[CHR7-CHR8-O]q-, les radicaux -O-CH2-CH2-, -CH2-CH(CH3)-O-,
- CH(CH3)-CH2-O-, -CH(C2H5)-CH2-O- ou -CH2-CH(C2H5)-O-, sont distribués de façon séquencée ou aléatoire.Within each of the groups - [O-CHR 1 -CHR 2 ] n -, - [CHR 3 -CHR 4 -O] m -, - [CHR 5 -CHR 6 -O] p - or - [CHR 7 - CHR 8 -O] q -, the radicals -O-CH 2 -CH 2 -, -CH 2 -CH (CH 3 ) -O-,
- CH (CH 3 ) -CH 2 -O-, -CH (C 2 H 5 ) -CH 2 -O- or -CH 2 -CH (C 2 H 5 ) -O-, are distributed sequentially or randomly .

Selon un aspect particulier, l'invention a pour objet une composition telle que définie précédemment, pour laquelle dans la formule(I), R1, R2, R3 et R4, représentent chacun un atome d'hydrogène.According to a particular aspect, the subject of the invention is a composition as defined above, for which, in the formula (I), R 1 , R 2 , R 3 and R 4 each represent a hydrogen atom.

Selon un autre aspect particulier, l'invention a pour objet une composition telle que définie précédemment, pour laquelle dans la formule(II), R4, R5, R6 et R7, représentent chacun un atome d'hydrogène.According to another particular aspect, the subject of the invention is a composition as defined above, for which, in formula (II), R 4 , R 5 , R 6 and R 7 each represent a hydrogen atom.

Selon encore un autre aspect particulier, l'invention a pour objet une composition telle que définie précédemment, comprenant de 10 % en poids à 60% en poids et de préférence de 15% en poids à 55 % en poids de composé de formule (I) et de 40% en poids à 90 % en poids et de préférence de 45 % en poids à 85 % en poids de composé de formule (II).According to yet another particular aspect, the subject of the invention is a composition as defined above, comprising from 10% by weight to 60% by weight and preferably from 15% by weight to 55% by weight of compound of formula (I) and from 40% by weight to 90% by weight and preferably from 45% by weight to 85% by weight of compound of formula (II).

L'invention a tout particulièrement pour objet une composition telle que définie précédemment dans laquelle le composé de formule (I) est :le bisphénol A diéthoxylé de formule (Ia) :

Figure 00040001
et dans laquelle le composé de formule (II) est le résorcinol diéthoxylé de formule (IIa) !
Figure 00040002
et de préférence pour objet une composition contenant de 30 % en poids à 50% en poids de composé de formule (Ia) et de 50% en poids à 70% en poids de composé de formule (IIa).The subject of the invention is particularly a composition as defined above in which the compound of formula (I) is: diethoxylated bisphenol A of formula (Ia):
Figure 00040001
and wherein the compound of formula (II) is diethoxylated resorcinol of formula (IIa)!
Figure 00040002
and preferably a composition containing from 30% by weight to 50% by weight of compound of formula (Ia) and from 50% by weight to 70% by weight of compound of formula (IIa).

Selon un autre aspect, l'invention a aussi pour objet, l'utilisation de la composition telle que définie précédemment comme allongeur de chaíne dans une formulation élastomère de polyuréthannes ainsi qu'un procédé de préparation d'une formulation élastomère de polyuréthanne à partir de prépolymère isocyanate et d'une quantité efficace d'allongeur de chaíne, caractérisé en ce que ledit allongeur de chaíne est la composition telle que défmie précédemment. According to another aspect, the subject of the invention is also the use of the composition as defined previously as a chain extender in an elastomeric formulation of polyurethanes and a method for preparing an elastomeric formulation of polyurethane from isocyanate prepolymer and an effective amount of extender chain, characterized in that said chain extender is the composition as defmie previously.

Selon un dernier aspect, l'invention a pour objet, l'utilisation de la composition telle que définie précédemment, comme monomères dans la préparation de polyesters saturés ou insaturés, de polycarbonates ou de résines époxy.According to a last aspect, the subject of the invention is the use of the composition as defined above, as monomers in the preparation of saturated polyesters unsaturated, polycarbonates or epoxy resins.

L'exposé suivant illustre l'invention sans toutefois la limiter.The following description illustrates the invention without limiting it.

On prépare un mélange de 52 % en poids de résorcinol diéthoxylé et 48 % en poids de bisphénol A diéthoxylé dénommée composition E.A mixture of 52% by weight of diethoxylated resorcinol and 48% by weight of weight of diethoxylated bisphenol A called composition E.

On prépare ensuite deux compositions élastomères en polyuréthanne selon un mode expérimental connu de l'homme du métier dont les paramètres sont consignés dans le tableau 1 suivant, à partir du Vibrathane™ B625 qui est un prépolymère isocyanate ayant un pourcentage en fonction isocyanate (-N-C=O) compris entre 6,2 et 6,9, d'un allongeur de chaíne, le butanediol 1,4 pour la formulation A selon l'état de la technique ou la composition E pour la formulation I selon l'invention. Formulation Formulation A (base de comparaison) Formulation I (invention) Vibrathane™ B625 (% NCO : 6029) 100 g 100 Butanediol-1,4 6,41 g 0 composition E 0 7,39 g BYK™ A 530 (agent débullant) 0,5 g 0,5 g Durée de vie en pot 6 minutes 21 minutes Paramètres de procédé Température du prépolymère 85 °C 85 °C Température de l'allongeur 85 °C 85 °C Température de cuisson 120 °C 120 °C Temps d'agitation 30 minutes 30 minutes Temps de cuisson 4 heures 4 heures Temps de post cuisson 16 heures 16 heures temps de maturation 6 jours 6 jours Aspect de la formulation finale opaque légère transparence Température vitreuse - 69.7 °C -55,7 °C Température de fusion 169,2°C 157°C Two polyurethane elastomer compositions are then prepared according to an experimental method known to those skilled in the art, the parameters of which are given in the following Table 1, starting from Vibrathane ™ B625, which is an isocyanate prepolymer having a percentage based on isocyanate (-NC = O) between 6.2 and 6.9, of a chain extender, 1,4 butanediol for the formulation A according to the state of the art or composition E for the formulation I according to the invention. Formulation Formulation A (basis of comparison) Formulation I (invention) Vibrathane ™ B625 (% NCO: 6029) 100 g 100 1,4-butanediol 6.41 g 0 composition E 0 7.39 g BYK ™ A 530 (debulling agent) 0.5 g 0.5 g Pot life 6 minutes 21 minutes Process parameters Prepolymer temperature 85 ° C 85 ° C Extender temperature 85 ° C 85 ° C Cooking temperature 120 ° C 120 ° C Stirring time 30 minutes 30 minutes Cooking time 4 hours 4 hours Post cooking time 16 hours 16 hours ripening time 6 days 6 days Aspect of the final formulation opaque slight transparency Glassy temperature 69.7 ° C -55.7 ° C Melting temperature 169.2 ° C 157 ° C

On évalue les propriétés mécaniques de chacune des formulations A et I, avant vieillissement, après vieillissement en étuve sèche et après vieillissement en étuve humide.The mechanical properties of each of the formulations A and I are evaluated before aging, after aging in a drying oven and after aging in a humid oven.

les résultats sont consignés dans les tableaux 2, 3 et 4 suivants Tableau 2 : Propriétés mécaniques avant vieillissement Formulation A (comparaison) Formulation I (invention) Dureté (selon la norme ISO 868) 84 87 Propriétés en traction (selon la norme ISO 37) Contrainte à 100 % 6,15 MPa 7,34 MPa Contrainte à 200 % 9,16 MPa 10,11 MPa Contrainte à 300 % 12,78 MPa 12,93 MPa Contrainte à la rupture 20,01 MPa 18,15 MPa Elongation à la rupture 450 % 485 % Module d'Young 16,88 MPa 22.15 MPa Résistance à la déchirure (selon la norme ISO 34) 44,43 kN/m 69,63 kN/m Résistance à l'abrasion (selon la norme ISO 9352) 0,05 % 0,17 % Densité (selon la norme ISO 1183) 1,03 1,04 Rebond (selon la norme ISO 4662) 69 60 Propriétés mécaniques après vieillissement en étuve sèche Formulation A Formulation I (comparaison) (invention) Vieillissement de 400 heures à 110 °C Aspect de l'élastomère brun foncé, opaque jaune, légèrement transparente Dureté (selon la norme ISO 868) 78 84 Propriétés en traction (selon la norme ISO 37) Contrainte à 100 % 4,06 MPa 5,80 MPa Contrainte à 200 % 5,63 MPa 7,15 MPa Contrainte à la rupture 6,55 MPa 8.35 MPa Elongation à la rupture 270 % 290 % Module d'Young 11,32 MPa 20,74 MPa Aspect de l'élastomère brun très foncé opaque brun, légèrement transparente Dureté (selon la norme ISO 868) 74 84 Propriétés en traction (selon la norme ISO 37) Contrainte à 100 % 3,45 MPa 5.44 MPa Contrainte à 200 % 4,86 MPa 6,24 MPa Contrainte à la rupture 5,53 MPa 6,27 MPa Elongation à la rupture 230 % 202 % Module d'Young 9,86 MPa 19,68 MPa Résistance à la déchirure (selon la norme ISO 34) 22,45 kN/m 41,63 kN/m Propriétés mécaniques après vieillissement en étuve humide Formulation A (comparaison) Formulation I (invention) Vieillissement de 400 heures à 70 °C ; humidité : 98 % Aspect de l'élastomère jaune légèrement jaune Dureté (selon la norme ISO 868) 81 87 Propriétés en traction (selon la norme ISO 37) Contrainte à 100 % 5,13 MPa 6,49 MPa Contrainte à 200 % 7,83 MPa 9,18 MPa Contrainte à 300 % 10,87 MPa 11,70 MPa Contrainte à la rupture 17,08 MPa 16,79 MPa Elongation à la rupture 440 % 500 % Module d'Young 13,57 MPa 19,09 MPa Aspect de l'élastomère jaune légèrement jaune Dureté (selon la norme ISO 868) 80 87 Propriétés en traction (selon la norme ISO 37) Contrainte à 100 % 5,07 MPa 5.44 MPa Contrainte à 200 % 7,56 MPa 6,24 MPa Contrainte à 300 % 10,77 MPa 6,27 MPa Contrainte à la rupture 17,50 MPa 16,84 MPa Elongation à la rupture 440 % 500 % Module d'Young 13,38 MPa 41,63 MPa Résistance à la déchirure (selon la norme ISO 34) 37,68 kN/m 62.50 kN/m the results are recorded in the following tables 2, 3 and 4 Table 2: Mechanical properties before aging Formulation A (comparison) Formulation I (invention) Hardness (according to ISO 868) 84 87 Tensile properties (according to ISO 37) 100% constraint 6.15 MPa 7.34 MPa 200% constraint 9.16 MPa 10.11 MPa 300% constraint 12.78 MPa 12.93 MPa Stress at break 20.01 MPa 18.15 MPa Elongation at break 450% 485% Young's module 16.88 MPa 22.15 MPa Tear resistance (according to ISO 34) 44.43 kN / m 69.63 kN / m Abrasion resistance (according to ISO 9352) 0.05% 0.17% Density (according to ISO 1183) 1.03 1.04 Rebound (according to ISO 4662) 69 60 Mechanical properties after aging in a drying oven Formulation A Formulation I (comparison) (invention) Aging 400 hours at 110 ° C Aspect of the elastomer dark brown, opaque yellow, slightly transparent Hardness (according to ISO 868) 78 84 Tensile properties (according to ISO 37) 100% constraint 4.06 MPa 5.80 MPa 200% constraint 5.63 MPa 7.15 MPa Stress at break 6.55 MPa 8.35 MPa Elongation at break 270% 290% Young's module 11.32 MPa 20.74 MPa Aspect of the elastomer very dark brown opaque brown, slightly transparent Hardness (according to ISO 868) 74 84 Tensile properties (according to ISO 37) 100% constraint 3.45 MPa 5.44 MPa 200% constraint 4.86 MPa 6.24 MPa Stress at break 5.53 MPa 6.27 MPa Elongation at break 230% 202% Young's module 9.86 MPa 19.68 MPa Tear resistance (according to ISO 34) 22.45 kN / m 41.63 kN / m Mechanical properties after aging in a humid oven Formulation A (comparison) Formulation I (invention) Aging 400 hours at 70 ° C; humidity: 98% Aspect of the elastomer yellow slightly yellow Hardness (according to ISO 868) 81 87 Tensile properties (according to ISO 37) 100% constraint 5.13 MPa 6.49 MPa 200% constraint 7.83 MPa 9.18 MPa 300% constraint 10.87 MPa 11.70 MPa Stress at break 17.08 MPa 16.79 MPa Elongation at break 440% 500% Young's module 13.57 MPa 19.09 MPa Aspect of the elastomer yellow slightly yellow Hardness (according to ISO 868) 80 87 Tensile properties (according to ISO 37) 100% constraint 5.07 MPa 5.44 MPa 200% constraint 7.56 MPa 6.24 MPa 300% constraint 10.77 MPa 6.27 MPa Stress at break 17.50 MPa 16.84 MPa Elongation at break 440% 500% Young's module 13.38 MPa 41.63 MPa Tear resistance (according to ISO 34) 37.68 kN / m 62.50 kN / m

Ces résultats font clairement apparaítre l'intérêt qu'il y a à utiliser la composition E selon l'invention comme allongeur de chaíne par rapport au butanediol-1,4, le produit le plus utilisé dans cette fonction.These results clearly show the interest in using the composition E according to the invention as a chain extender with respect to butanediol-1,4, the product the more used in this function.

Claims (9)

Composition caractérisée en ce qu'elle comprend : de 0,5 % en poids à 100 % d'un composé de formule (I) :
Figure 00090001
 dans laquelle R1, R2, R3 et R4 identiques ou différents, représentent indépendamment, les uns des autres un atome d'hydrogène, un radical méthyle ou un radical éthyle,
n et m identiques ou différents, représentent indépendamment l'un de l'autre un nombre compris entre 0 et 10 étant entendu que la somme n + m est supérieure à zéro,
et de 0% à 99,5 % en poids d'un composé de formule (II) :
Figure 00090002
 dans laquelle R5, R6, R7 et R8 identiques ou différents, représentent indépendamment, les uns des autres un atome d'hydrogène, un radical méthyle ou un radical éthyle,
p et q identiques ou différents, représentent indépendamment l'un de l'autre un nombre compris entre 0 et 10 étant entendu que la somme p + q est supérieure à zéro. Composition characterized in that it comprises: from 0.5% by weight to 100% of a compound of formula (I):
Figure 00090001
 in which R 1 , R 2 , R 3 and R 4, which are identical or different, independently of one another represent a hydrogen atom, a methyl radical or an ethyl radical,
n and m, which are identical or different, represent, independently of one another, a number between 0 and 10, provided that the sum n + m is greater than zero,
and from 0% to 99.5% by weight of a compound of formula (II):
Figure 00090002
 in which R 5 , R 6 , R 7 and R 8, which are identical or different, independently of one another represent a hydrogen atom, a methyl radical or an ethyl radical,
p and q identical or different, independently of each other represent a number between 0 and 10 provided that the sum p + q is greater than zero. Composition telle que défmie précédemment, pour laquelle dans la formule(I), R1, R2, R3 et R4, représentent chacun un atome d'hydrogène.Composition as defined above, for which in the formula (I), R 1 , R 2 , R 3 and R 4 each represent a hydrogen atom. Composition telle que définie à l'une des revendications 1 ou 2, pour laquelle dans la formule(II), R4, R5, R6 et R7, représentent chacun un atome d'hydrogène.Composition as defined in one of claims 1 or 2, wherein in formula (II), R 4 , R 5 , R 6 and R 7 , each represent a hydrogen atom. Composition telle que défmie à l'une des revendications 1 à 3, comprenant de 10 % en poids à 60% en poids et de préférence de 15% en poids à 55 % en poids de composé de formule (I) et de 40% en poids à 90 % en poids et de préférence de 45 % en poids à 85 % en poids de composé de formule (II).Composition as defined in one of Claims 1 to 3, comprising from 10% by weight to 60% by weight and preferably from 15% by weight to 55% by weight of compound of formula (I) and from 40% by weight to 90% by weight and preferably 45% by weight weight at 85% by weight of compound of formula (II). Composition telle que définie à l'une des revendications 1 à 4, dans laquelle le composé de formule (I) est :le bisphénol A diéthoxylé de formule (Ia) :
Figure 00100001
et dans laquelle le composé de formule (II) est le résorcinol diéthoxylé de formule (IIa) !
Figure 00100002
Composition as defined in one of Claims 1 to 4, in which the compound of formula (I) is: diethoxylated bisphenol A of formula (Ia):
Figure 00100001
and wherein the compound of formula (II) is diethoxylated resorcinol of formula (IIa)!
Figure 00100002
 Composition telle que défmie à la revendication 5, contenant de 30 % en poids à 50 % en poids de composé de formule (Ia) et de 50 % en poids à 70 % en poids de composé de formule (IIa).Composition as defined in claim 5, containing 30% by weight weight at 50% by weight of compound of formula (Ia) and from 50% by weight to 70% by weight of compound of formula (IIa). Utilisation de la composition telle que définie à l'une des revendications 1 à 6, comme allongeurs de chaíne dans une formulation élastomère de polyuréthannes.Use of the composition as defined in one of claims 1 at 6, as chain extenders in an elastomeric formulation of polyurethanes. Procédé de préparation d'une formulation élastomère de polyuréthanne à partir de prépolymère isocyanate et d'une quantité efficace d'allongeur de chaíne, caractérisé en ce que ledit allongeur de chaíne est la composition telle que définie à l'une des revendications 1 à 6.Process for the preparation of a polyurethane elastomer formulation from an isocyanate prepolymer and an effective amount of chain extender, characterized in that said chain extender is the composition as defined in one of claims 1 to 6 . Utilisation de la composition telle que définie à l'une des revendications 1 à 6, comme monomères dans la préparation de polyesters saturés ou insaturés, de polycarbonates ou de résines époxy.Use of the composition as defined in one of claims 1 to 6, as monomers in the preparation of saturated or unsaturated polyesters, polycarbonates or epoxy resins.
EP04102986A 2003-07-11 2004-06-28 Use of a mixture of bisethoxylated bisphenol a / diethoxylated resorcinol (dianol 220/HER) as chain extender for polyurethane elastomers compositions Withdrawn EP1496074A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0350323 2003-07-11
FR0350323A FR2857366B1 (en) 2003-07-11 2003-07-11 USE OF A DIANOL 220 / HER MIXTURE AS A CHAIN FASTENER OF ELASTOMERIC POLYURETHANE FORMULATIONS

Publications (1)

Publication Number Publication Date
EP1496074A1 true EP1496074A1 (en) 2005-01-12

Family

ID=33443297

Family Applications (1)

Application Number Title Priority Date Filing Date
EP04102986A Withdrawn EP1496074A1 (en) 2003-07-11 2004-06-28 Use of a mixture of bisethoxylated bisphenol a / diethoxylated resorcinol (dianol 220/HER) as chain extender for polyurethane elastomers compositions

Country Status (4)

Country Link
US (1) US20050192422A1 (en)
EP (1) EP1496074A1 (en)
JP (1) JP2005048169A (en)
FR (1) FR2857366B1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2927903A1 (en) * 2008-02-25 2009-08-28 Seppic Sa NOVEL CHAIN EXTENSIONS FOR FORMULATIONS OF ELASTOMERS OF POLYURETHANES.
WO2013034867A1 (en) 2011-09-08 2013-03-14 Cecalc Improvement of the physical properties of polyurethane polymers

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10640475B2 (en) 2017-09-22 2020-05-05 Hexion Inc. Compositions and methods to produce alkoxylated triazine-arlhydroxy-aldehyde condensates
US10435503B2 (en) 2017-09-22 2019-10-08 Hexion Inc. Compositions for polyurethane applications
US10604614B2 (en) 2017-09-22 2020-03-31 Hexion Inc. Compositions and methods to produce alkoxylated triazine-arylhydroxy-aldehyde condensates
CN114621577B (en) * 2022-03-22 2023-09-01 浙江伟星实业发展股份有限公司 Anti-color-absorption resin material and preparation method and application thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4268647A (en) * 1978-12-06 1981-05-19 General Electric Company Organic materials having meta, para-isopropylidene diphenoxy units and method
US4442281A (en) * 1982-09-08 1984-04-10 Akzo Nv Thermoplastic polyurethane-elastomers from cyclohexane-1,4-diisocyanate
JPH02214727A (en) * 1989-02-14 1990-08-27 Mitsubishi Kasei Corp Aromatic polyesteramide and production thereof
US5216107A (en) * 1990-07-17 1993-06-01 Bayer Aktiengesellschaft Binder compositions for stoving lacquers and a process for the production of coatings therefrom

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3829505A (en) * 1970-02-24 1974-08-13 Gen Tire & Rubber Co Polyethers and method for making the same
JP2928266B2 (en) * 1989-05-08 1999-08-03 ポリプラスチックス株式会社 Polyester resin composition and molded article
DE19626567A1 (en) * 1996-07-03 1998-01-08 Basf Ag Polyurethanes
DE10138765A1 (en) * 2001-08-07 2003-02-20 Bayer Ag Aqueous dispersions of hydrophilic polyurethane resins
DE10219028A1 (en) * 2002-04-29 2003-11-06 Bayer Ag Production and use of high molecular weight aliphatic polycarbonates

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4268647A (en) * 1978-12-06 1981-05-19 General Electric Company Organic materials having meta, para-isopropylidene diphenoxy units and method
US4442281A (en) * 1982-09-08 1984-04-10 Akzo Nv Thermoplastic polyurethane-elastomers from cyclohexane-1,4-diisocyanate
JPH02214727A (en) * 1989-02-14 1990-08-27 Mitsubishi Kasei Corp Aromatic polyesteramide and production thereof
US5216107A (en) * 1990-07-17 1993-06-01 Bayer Aktiengesellschaft Binder compositions for stoving lacquers and a process for the production of coatings therefrom

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 014, no. 513 (C - 0777) 9 November 1990 (1990-11-09) *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2927903A1 (en) * 2008-02-25 2009-08-28 Seppic Sa NOVEL CHAIN EXTENSIONS FOR FORMULATIONS OF ELASTOMERS OF POLYURETHANES.
WO2009106774A1 (en) * 2008-02-25 2009-09-03 Societe D'exploitation De Produits Pour Les Industries Chimiques Seppic Novel chain elongators for polyurethane elastomer compositions
WO2013034867A1 (en) 2011-09-08 2013-03-14 Cecalc Improvement of the physical properties of polyurethane polymers

Also Published As

Publication number Publication date
JP2005048169A (en) 2005-02-24
FR2857366A1 (en) 2005-01-14
US20050192422A1 (en) 2005-09-01
FR2857366B1 (en) 2007-08-10

Similar Documents

Publication Publication Date Title
US4879402A (en) (Methyl)acrylic acid derivatives containing urethane groups
EP1784442B1 (en) Crosslinkable siloxane urea copolymers
US4490300A (en) Liquid diphenylmethane diisocyanate compositions
LU81024A1 (en) PROCESS FOR THE PREPARATION OF FULL-SKIN POLYURETHANE AND POLYURETHANE OBTAINED
EP0254185A1 (en) (Meth)acrylic acid derivatives of tricyclo[5.2.1.02.6]decanes containing urethane groups
EP0007265A1 (en) Unsaturated polycarbonate-urethanes utilizable in photoreticulation compositions; film obtained from such a composition
EP0109342A1 (en) Moulding compositions of semi-rigid copolyamides derived from dimeric fatty acids, elastomers and optionally conventional polyamides
CN1257520A (en) Silicon-based polycarbonates
FR2601024A1 (en) STORAGE-STABLE POLYOL MIXTURE, PROCESS FOR PREPARING SAME, PROCESS FOR PREPARING POLYURETHANE USING THE SAME, AND POLYOL ADDITION PRODUCT USEFUL FOR SAME
FR2472585A1 (en) PROCESS FOR THE PRODUCTION OF POLYMER POLYOLS AND THE USE THEREOF FOR THE MANUFACTURE OF POLYURETHANE
EP1496074A1 (en) Use of a mixture of bisethoxylated bisphenol a / diethoxylated resorcinol (dianol 220/HER) as chain extender for polyurethane elastomers compositions
CA2192852C (en) Plastified composition containing a controlled viscosity polyol
FR2588009A1 (en) PROCESS FOR THE PREPARATION OF AQUEOUS BITUMEN-POLYURETHANE EMULSION COMPOSITION
BE1010655A3 (en) Compositions polyamides plasticized.
EP0963389B1 (en) Photopolymerisable composition based on polyiso(thio)cyanate monomers and monomers with labile proton, comprising a photoinitiator and an agent activating polymerisation and resulting optical articles
CN102807539A (en) Resin system capable of realizing automatic oxidation, automatic initiation and radiation curing and preparation method thereof
EP2247635B1 (en) Novel chain elongators for polyurethane elastomer compositions
EP0156665A1 (en) Process for the modification of the hydrolysis resistance of saturated urethane elastomers, compositions for carrying out this process and products obtained
FR2518555A1 (en) COMPOSITIONS OF POLYURETHANE RESINS WITH LATENT HARDENERS
EP0748838A1 (en) Porphyrin-containing silicones with improved temperature resistance
EP0263749B1 (en) Process for the preparation of radiocrosslinked coatings
FR2513646A1 (en) STABILIZED SYNTHETIC RESIN COMPOSITION
DE69934568D1 (en) Coating compositions containing a mixture of ethylenically unsaturated polyurethanes
CA2037734A1 (en) Polyester/silicone coreticulate degradable by hydrolysis
EP3861039B1 (en) Hydrogel compositions

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LI LU MC NL PL PT RO SE SI SK TR

AX Request for extension of the european patent

Extension state: AL HR LT LV MK

17P Request for examination filed

Effective date: 20050712

AKX Designation fees paid

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LI LU MC NL PL PT RO SE SI SK TR

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20101231